Bis[(2-quinol-yl)methane-diol-κN,O](sulfato-κO)copper(II) dihydrate.

In the title compound, [Cu(SO(4))(C(10)H(9)NO(2))(2)]·2H(2)O, the Cu(II) ion is chelated by two (2-quinol-yl)methane-diol ligands and coordinated by a monodentate sulfate ligand in a distorted trigonal-bipyramidal environment, with O atoms occupying the equatorial sites and N atoms in the axial sites. The dihedral angle between the two essentially planar quinoline ring systems is 45.02 (9)°. In the crystal structure, an extensive O-H⋯O hydrogen-bonding network forms layers parallel to the ab plane.

Related literature

For related literature, see: Zurowska et al. (2007 ▶); Dobrzynska et al. (2005 ▶); Kumar & Gandotra (1980 ▶); Catterick et al. (1974 ▶).

Experimental

Crystal data

[Cu(SO4)(C10H9NO2)2]·2H2O

M = 546.00

Triclinic,

a = 7.6065 (3) Å

b = 8.8747 (4) Å

c = 17.5035 (9) Å

α = 98.561 (3)°

β = 94.324 (3)°

γ = 111.305 (2)°

V = 1077.76 (9) Å3

Z = 2

Mo Kα radiation

μ = 1.17 mm−1

T = 293 (2) K

0.24 × 0.15 × 0.12 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.810, T max = 0.864

18073 measured reflections

5289 independent reflections

3972 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.090

S = 1.00

5289 reflections

331 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001980/lh2587sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001980/lh2587Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(SO4)(C10H9NO2)2]·2H2O	Z = 2
Mr = 546.00	F000 = 562
Triclinic, P1	Dx = 1.682 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.6065 (3) Å	Cell parameters from 4898 reflections
b = 8.8747 (4) Å	θ = 2.4–27.5º
c = 17.5035 (9) Å	µ = 1.17 mm−1
α = 98.561 (3)º	T = 293 (2) K
β = 94.324 (3)º	Block, green
γ = 111.305 (2)º	0.24 × 0.15 × 0.12 mm
V = 1077.76 (9) Å3

Bruker APEX CCD area-detector diffractometer	5289 independent reflections
Radiation source: fine-focus sealed tube	3972 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.037
T = 293(2) K	θmax = 28.4º
φ and ω scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)	h = −10→10
Tmin = 0.810, Tmax = 0.864	k = −11→11
18073 measured reflections	l = −23→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0404P)2 + 0.5543P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
5289 reflections	Δρmax = 0.36 e Å−3
331 parameters	Δρmin = −0.34 e Å−3
8 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cu1	0.34983 (4)	0.15697 (4)	0.247112 (17)	0.02622 (9)
S1	0.62616 (8)	−0.03258 (7)	0.26884 (3)	0.02588 (14)
O1	0.0893 (2)	−0.0211 (3)	0.26309 (11)	0.0385 (4)
H1A	−0.017 (3)	−0.040 (4)	0.2454 (19)	0.058*
O2	0.1228 (3)	−0.2200 (3)	0.32675 (13)	0.0452 (5)
H2A	0.233 (3)	−0.201 (4)	0.315 (2)	0.068*
O3	0.3080 (3)	0.3702 (2)	0.24886 (10)	0.0349 (4)
H3A	0.198 (3)	0.362 (4)	0.2561 (18)	0.052*
O4	0.4924 (4)	0.5501 (3)	0.17828 (14)	0.0576 (6)
H4A	0.499 (6)	0.631 (4)	0.2102 (19)	0.086*
O5	0.5547 (3)	0.0768 (2)	0.22997 (10)	0.0365 (4)
O6	0.7384 (2)	−0.0907 (2)	0.21500 (10)	0.0350 (4)
O7	0.4641 (3)	−0.1762 (2)	0.27989 (12)	0.0427 (5)
O8	0.7444 (3)	0.0593 (2)	0.34206 (10)	0.0378 (4)
N1	0.3830 (3)	0.1802 (3)	0.36291 (11)	0.0264 (4)
N2	0.2914 (3)	0.1435 (2)	0.13256 (11)	0.0262 (4)
C1	0.0981 (4)	−0.0705 (3)	0.33518 (15)	0.0336 (6)
H1	−0.0220	−0.0846	0.3558	0.040*
C2	0.2594 (3)	0.0620 (3)	0.39163 (14)	0.0297 (5)
C3	0.2741 (4)	0.0530 (4)	0.47104 (16)	0.0374 (6)
H3	0.1860	−0.0336	0.4888	0.045*
C4	0.4189 (4)	0.1726 (4)	0.52174 (15)	0.0389 (6)
H4	0.4306	0.1684	0.5746	0.047*
C5	0.5511 (4)	0.3028 (3)	0.49378 (14)	0.0316 (6)
C6	0.5303 (3)	0.3033 (3)	0.41296 (14)	0.0272 (5)
C7	0.6616 (4)	0.4320 (3)	0.38398 (15)	0.0338 (6)
H7	0.6501	0.4327	0.3308	0.041*
C8	0.8053 (4)	0.5555 (4)	0.43358 (17)	0.0399 (6)
H8	0.8911	0.6401	0.4138	0.048*
C9	0.8259 (4)	0.5572 (4)	0.51402 (17)	0.0424 (7)
H9	0.9242	0.6428	0.5472	0.051*
C10	0.7021 (4)	0.4336 (4)	0.54333 (16)	0.0399 (7)
H10	0.7168	0.4350	0.5967	0.048*
C11	0.3207 (4)	0.4235 (3)	0.17647 (15)	0.0356 (6)
H11	0.2168	0.4609	0.1651	0.043*
C12	0.3067 (3)	0.2843 (3)	0.11182 (14)	0.0292 (5)
C13	0.3066 (4)	0.3061 (3)	0.03416 (15)	0.0380 (6)
H13	0.3209	0.4079	0.0219	0.046*
C14	0.2855 (4)	0.1769 (4)	−0.02309 (15)	0.0403 (7)
H14	0.2884	0.1905	−0.0747	0.048*
C15	0.2594 (4)	0.0225 (3)	−0.00399 (15)	0.0333 (6)
C16	0.2611 (3)	0.0077 (3)	0.07554 (14)	0.0275 (5)
C17	0.2298 (4)	−0.1460 (3)	0.09590 (16)	0.0365 (6)
H17	0.2320	−0.1566	0.1480	0.044*
C18	0.1964 (4)	−0.2788 (4)	0.03934 (18)	0.0449 (7)
H18	0.1718	−0.3809	0.0532	0.054*
C19	0.1977 (4)	−0.2669 (4)	−0.03936 (18)	0.0472 (7)
H19	0.1777	−0.3595	−0.0769	0.057*
C20	0.2283 (4)	−0.1192 (4)	−0.06075 (16)	0.0432 (7)
H20	0.2288	−0.1113	−0.1131	0.052*
O9	0.8632 (4)	0.5358 (4)	0.20715 (17)	0.0759 (8)
H91	0.935 (6)	0.628 (4)	0.236 (2)	0.114*
H92	0.750 (4)	0.541 (6)	0.197 (3)	0.114*
O10	−0.0100 (3)	0.3450 (3)	0.28886 (17)	0.0614 (6)
H101	−0.053 (6)	0.390 (5)	0.256 (2)	0.092*
H102	−0.088 (5)	0.264 (4)	0.304 (2)	0.092*

	U11	U22	U33	U12	U13	U23
Cu1	0.03079 (17)	0.03437 (18)	0.01980 (15)	0.01816 (14)	0.00474 (12)	0.00847 (12)
S1	0.0268 (3)	0.0326 (3)	0.0227 (3)	0.0163 (3)	0.0031 (2)	0.0060 (2)
O1	0.0246 (9)	0.0599 (13)	0.0313 (10)	0.0131 (9)	0.0024 (8)	0.0180 (9)
O2	0.0360 (11)	0.0419 (11)	0.0577 (13)	0.0124 (9)	0.0078 (10)	0.0147 (10)
O3	0.0468 (11)	0.0420 (11)	0.0265 (9)	0.0280 (10)	0.0062 (8)	0.0085 (8)
O4	0.0752 (16)	0.0319 (12)	0.0560 (15)	0.0091 (12)	0.0173 (13)	0.0046 (10)
O5	0.0427 (10)	0.0520 (12)	0.0331 (10)	0.0338 (9)	0.0136 (8)	0.0185 (9)
O6	0.0350 (10)	0.0490 (11)	0.0279 (9)	0.0267 (9)	0.0036 (8)	0.0009 (8)
O7	0.0376 (10)	0.0382 (11)	0.0514 (12)	0.0114 (9)	0.0109 (9)	0.0109 (9)
O8	0.0420 (10)	0.0446 (11)	0.0263 (10)	0.0200 (9)	−0.0020 (8)	−0.0007 (8)
N1	0.0295 (10)	0.0361 (12)	0.0212 (10)	0.0189 (9)	0.0077 (8)	0.0098 (9)
N2	0.0284 (10)	0.0299 (11)	0.0232 (10)	0.0138 (9)	0.0033 (8)	0.0073 (9)
C1	0.0284 (13)	0.0435 (16)	0.0345 (14)	0.0155 (12)	0.0105 (11)	0.0164 (12)
C2	0.0320 (13)	0.0385 (14)	0.0273 (13)	0.0203 (12)	0.0089 (11)	0.0118 (11)
C3	0.0447 (16)	0.0439 (16)	0.0328 (15)	0.0210 (13)	0.0145 (13)	0.0204 (13)
C4	0.0539 (17)	0.0504 (17)	0.0229 (13)	0.0291 (15)	0.0084 (12)	0.0133 (13)
C5	0.0387 (14)	0.0424 (15)	0.0229 (12)	0.0255 (13)	0.0052 (11)	0.0071 (11)
C6	0.0290 (12)	0.0372 (14)	0.0220 (12)	0.0201 (11)	0.0063 (10)	0.0052 (11)
C7	0.0369 (14)	0.0427 (15)	0.0261 (13)	0.0182 (12)	0.0105 (11)	0.0085 (12)
C8	0.0355 (14)	0.0413 (16)	0.0426 (16)	0.0140 (13)	0.0085 (13)	0.0078 (13)
C9	0.0399 (16)	0.0475 (17)	0.0391 (16)	0.0216 (14)	−0.0015 (13)	−0.0037 (14)
C10	0.0467 (16)	0.0537 (18)	0.0256 (14)	0.0299 (15)	−0.0012 (12)	0.0018 (13)
C11	0.0486 (16)	0.0365 (15)	0.0318 (14)	0.0248 (13)	0.0079 (12)	0.0135 (12)
C12	0.0319 (13)	0.0347 (14)	0.0264 (13)	0.0176 (11)	0.0042 (10)	0.0088 (11)
C13	0.0501 (16)	0.0392 (15)	0.0312 (14)	0.0204 (13)	0.0085 (12)	0.0160 (12)
C14	0.0501 (17)	0.0518 (18)	0.0219 (13)	0.0197 (14)	0.0080 (12)	0.0135 (13)
C15	0.0326 (13)	0.0415 (15)	0.0243 (13)	0.0133 (12)	0.0022 (10)	0.0045 (11)
C16	0.0272 (12)	0.0334 (13)	0.0225 (12)	0.0135 (11)	0.0013 (10)	0.0034 (10)
C17	0.0467 (16)	0.0333 (14)	0.0299 (14)	0.0162 (13)	0.0008 (12)	0.0066 (12)
C18	0.0548 (18)	0.0315 (15)	0.0453 (18)	0.0158 (14)	0.0011 (14)	0.0028 (13)
C19	0.0548 (19)	0.0419 (17)	0.0369 (16)	0.0170 (15)	−0.0004 (14)	−0.0092 (14)
C20	0.0490 (17)	0.0507 (18)	0.0245 (14)	0.0165 (15)	0.0019 (12)	−0.0013 (13)
O9	0.080 (2)	0.0642 (17)	0.0698 (19)	0.0223 (16)	−0.0045 (16)	−0.0083 (14)
O10	0.0448 (13)	0.0588 (16)	0.0801 (19)	0.0174 (12)	0.0190 (13)	0.0126 (14)

Cu1—O5	1.9589 (16)	C6—C7	1.407 (3)
Cu1—N1	1.9938 (19)	C7—C8	1.361 (4)
Cu1—N2	1.9969 (19)	C7—H7	0.9300
Cu1—O3	2.0258 (17)	C8—C9	1.402 (4)
Cu1—O1	2.1080 (19)	C8—H8	0.9300
S1—O8	1.4486 (19)	C9—C10	1.357 (4)
S1—O7	1.4664 (19)	C9—H9	0.9300
S1—O6	1.4766 (17)	C10—H10	0.9300
S1—O5	1.4914 (17)	C11—C12	1.512 (4)
O1—C1	1.401 (3)	C11—H11	0.9800
O1—H1A	0.79 (2)	C12—C13	1.401 (3)
O2—C1	1.394 (3)	C13—C14	1.358 (4)
O2—H2A	0.84 (2)	C13—H13	0.9300
O3—C11	1.415 (3)	C14—C15	1.407 (4)
O3—H3A	0.83 (2)	C14—H14	0.9300
O4—C11	1.373 (3)	C15—C20	1.414 (4)
O4—H4A	0.83 (2)	C15—C16	1.417 (3)
N1—C2	1.322 (3)	C16—C17	1.402 (3)
N1—C6	1.376 (3)	C17—C18	1.353 (4)
N2—C12	1.320 (3)	C17—H17	0.9300
N2—C16	1.381 (3)	C18—C19	1.398 (4)
C1—C2	1.512 (4)	C18—H18	0.9300
C1—H1	0.9800	C19—C20	1.360 (4)
C2—C3	1.402 (3)	C19—H19	0.9300
C3—C4	1.360 (4)	C20—H20	0.9300
C3—H3	0.9300	O9—H91	0.86 (2)
C4—C5	1.409 (4)	O9—H92	0.89 (2)
C4—H4	0.9300	O10—H101	0.86 (2)
C5—C6	1.412 (3)	O10—H102	0.84 (2)
C5—C10	1.414 (4)
O5—Cu1—N1	96.19 (7)	N1—C6—C5	120.6 (2)
O5—Cu1—N2	90.66 (7)	C7—C6—C5	119.2 (2)
N1—Cu1—N2	173.14 (8)	C8—C7—C6	120.2 (2)
O5—Cu1—O3	137.56 (8)	C8—C7—H7	119.9
N1—Cu1—O3	94.29 (7)	C6—C7—H7	119.9
N2—Cu1—O3	80.56 (7)	C7—C8—C9	121.0 (3)
O5—Cu1—O1	115.59 (8)	C7—C8—H8	119.5
N1—Cu1—O1	79.02 (8)	C9—C8—H8	119.5
N2—Cu1—O1	98.05 (8)	C10—C9—C8	119.9 (3)
O3—Cu1—O1	106.76 (8)	C10—C9—H9	120.1
O8—S1—O7	111.92 (12)	C8—C9—H9	120.1
O8—S1—O6	110.54 (10)	C9—C10—C5	120.9 (3)
O7—S1—O6	108.23 (11)	C9—C10—H10	119.6
O8—S1—O5	109.74 (11)	C5—C10—H10	119.6
O7—S1—O5	109.44 (11)	O4—C11—O3	110.7 (2)
O6—S1—O5	106.82 (10)	O4—C11—C12	107.5 (2)
C1—O1—Cu1	112.67 (15)	O3—C11—C12	110.4 (2)
C1—O1—H1A	111 (2)	O4—C11—H11	109.4
Cu1—O1—H1A	131 (2)	O3—C11—H11	109.4
C1—O2—H2A	106 (3)	C12—C11—H11	109.4
C11—O3—Cu1	113.40 (14)	N2—C12—C13	122.8 (2)
C11—O3—H3A	101 (2)	N2—C12—C11	116.6 (2)
Cu1—O3—H3A	113 (2)	C13—C12—C11	120.6 (2)
C11—O4—H4A	110 (3)	C14—C13—C12	119.4 (2)
S1—O5—Cu1	132.80 (11)	C14—C13—H13	120.3
C2—N1—C6	119.1 (2)	C12—C13—H13	120.3
C2—N1—Cu1	116.29 (17)	C13—C14—C15	119.7 (2)
C6—N1—Cu1	124.51 (16)	C13—C14—H14	120.1
C12—N2—C16	119.3 (2)	C15—C14—H14	120.1
C12—N2—Cu1	114.79 (16)	C14—C15—C20	122.9 (2)
C16—N2—Cu1	125.41 (15)	C14—C15—C16	118.5 (2)
O2—C1—O1	110.8 (2)	C20—C15—C16	118.6 (2)
O2—C1—C2	110.6 (2)	N2—C16—C17	120.2 (2)
O1—C1—C2	109.4 (2)	N2—C16—C15	120.2 (2)
O2—C1—H1	108.7	C17—C16—C15	119.6 (2)
O1—C1—H1	108.7	C18—C17—C16	119.6 (3)
C2—C1—H1	108.7	C18—C17—H17	120.2
N1—C2—C3	123.0 (2)	C16—C17—H17	120.2
N1—C2—C1	117.7 (2)	C17—C18—C19	121.9 (3)
C3—C2—C1	119.2 (2)	C17—C18—H18	119.1
C4—C3—C2	119.2 (3)	C19—C18—H18	119.1
C4—C3—H3	120.4	C20—C19—C18	119.7 (3)
C2—C3—H3	120.4	C20—C19—H19	120.1
C3—C4—C5	119.6 (2)	C18—C19—H19	120.1
C3—C4—H4	120.2	C19—C20—C15	120.5 (3)
C5—C4—H4	120.2	C19—C20—H20	119.7
C4—C5—C6	118.5 (2)	C15—C20—H20	119.7
C4—C5—C10	122.7 (2)	H91—O9—H92	107 (4)
C6—C5—C10	118.8 (2)	H101—O10—H102	118 (4)
N1—C6—C7	120.1 (2)
O5—Cu1—O1—C1	71.43 (18)	C2—N1—C6—C5	0.8 (3)
N1—Cu1—O1—C1	−20.23 (17)	Cu1—N1—C6—C5	−174.93 (16)
N2—Cu1—O1—C1	166.06 (17)	C4—C5—C6—N1	0.7 (3)
O3—Cu1—O1—C1	−111.44 (17)	C10—C5—C6—N1	−178.7 (2)
O5—Cu1—O3—C11	62.2 (2)	C4—C5—C6—C7	−179.7 (2)
N1—Cu1—O3—C11	166.21 (18)	C10—C5—C6—C7	0.9 (3)
N2—Cu1—O3—C11	−18.35 (18)	N1—C6—C7—C8	178.8 (2)
O1—Cu1—O3—C11	−113.98 (18)	C5—C6—C7—C8	−0.8 (3)
O8—S1—O5—Cu1	−78.16 (18)	C6—C7—C8—C9	0.1 (4)
O7—S1—O5—Cu1	45.01 (19)	C7—C8—C9—C10	0.5 (4)
O6—S1—O5—Cu1	161.97 (15)	C8—C9—C10—C5	−0.4 (4)
N1—Cu1—O5—S1	35.82 (18)	C4—C5—C10—C9	−179.7 (2)
N2—Cu1—O5—S1	−144.19 (17)	C6—C5—C10—C9	−0.4 (4)
O3—Cu1—O5—S1	139.14 (15)	Cu1—O3—C11—O4	−103.0 (2)
O1—Cu1—O5—S1	−44.94 (19)	Cu1—O3—C11—C12	16.0 (3)
O5—Cu1—N1—C2	−101.70 (17)	C16—N2—C12—C13	−4.5 (4)
O3—Cu1—N1—C2	119.48 (17)	Cu1—N2—C12—C13	167.7 (2)
O1—Cu1—N1—C2	13.22 (16)	C16—N2—C12—C11	174.3 (2)
O5—Cu1—N1—C6	74.10 (18)	Cu1—N2—C12—C11	−13.5 (3)
O3—Cu1—N1—C6	−64.71 (18)	O4—C11—C12—N2	119.0 (2)
O1—Cu1—N1—C6	−170.97 (18)	O3—C11—C12—N2	−1.9 (3)
O5—Cu1—N2—C12	−120.78 (17)	O4—C11—C12—C13	−62.2 (3)
O3—Cu1—N2—C12	17.49 (17)	O3—C11—C12—C13	176.9 (2)
O1—Cu1—N2—C12	123.25 (17)	N2—C12—C13—C14	1.6 (4)
O5—Cu1—N2—C16	50.87 (19)	C11—C12—C13—C14	−177.1 (3)
O3—Cu1—N2—C16	−170.9 (2)	C12—C13—C14—C15	1.6 (4)
O1—Cu1—N2—C16	−65.10 (19)	C13—C14—C15—C20	177.2 (3)
Cu1—O1—C1—O2	−99.7 (2)	C13—C14—C15—C16	−1.7 (4)
Cu1—O1—C1—C2	22.5 (2)	C12—N2—C16—C17	−175.1 (2)
C6—N1—C2—C3	−1.9 (3)	Cu1—N2—C16—C17	13.6 (3)
Cu1—N1—C2—C3	174.13 (18)	C12—N2—C16—C15	4.2 (3)
C6—N1—C2—C1	179.38 (19)	Cu1—N2—C16—C15	−167.07 (17)
Cu1—N1—C2—C1	−4.6 (3)	C14—C15—C16—N2	−1.2 (4)
O2—C1—C2—N1	109.7 (2)	C20—C15—C16—N2	179.9 (2)
O1—C1—C2—N1	−12.5 (3)	C14—C15—C16—C17	178.1 (2)
O2—C1—C2—C3	−69.0 (3)	C20—C15—C16—C17	−0.8 (4)
O1—C1—C2—C3	168.7 (2)	N2—C16—C17—C18	178.6 (2)
N1—C2—C3—C4	1.6 (4)	C15—C16—C17—C18	−0.7 (4)
C1—C2—C3—C4	−179.8 (2)	C16—C17—C18—C19	2.0 (5)
C2—C3—C4—C5	0.0 (4)	C17—C18—C19—C20	−1.8 (5)
C3—C4—C5—C6	−1.1 (4)	C18—C19—C20—C15	0.2 (5)
C3—C4—C5—C10	178.3 (2)	C14—C15—C20—C19	−177.9 (3)
C2—N1—C6—C7	−178.8 (2)	C16—C15—C20—C19	1.0 (4)
Cu1—N1—C6—C7	5.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O6i	0.79 (3)	1.77 (3)	2.554 (2)	174 (4)
O3—H3A···O10	0.83 (3)	1.69 (3)	2.510 (3)	169 (3)
O4—H4A···O6ii	0.83 (3)	2.46 (4)	2.992 (3)	123 (3)
O4—H4A···O7ii	0.83 (3)	2.06 (4)	2.874 (3)	169 (5)
O9—H91···O2iii	0.86 (4)	2.00 (4)	2.810 (4)	157 (3)
O9—H92···O4	0.89 (4)	2.00 (4)	2.879 (5)	178 (6)
O10—H101···O9i	0.86 (4)	1.91 (4)	2.746 (4)	164 (4)
O10—H102···O8i	0.84 (3)	2.04 (3)	2.883 (3)	174 (4)

Table 1

Selected bond lengths (Å)

Cu1—O5	1.9589 (16)
Cu1—N1	1.9938 (19)
Cu1—N2	1.9969 (19)
Cu1—O3	2.0258 (17)
Cu1—O1	2.1080 (19)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O6i	0.79 (3)	1.77 (3)	2.554 (2)	174 (4)
O3—H3A⋯O10	0.83 (3)	1.69 (3)	2.510 (3)	169 (3)
O4—H4A⋯O6ii	0.83 (3)	2.46 (4)	2.992 (3)	123 (3)
O4—H4A⋯O7ii	0.83 (3)	2.06 (4)	2.874 (3)	169 (5)
O9—H91⋯O2iii	0.86 (4)	2.00 (4)	2.810 (4)	157 (3)
O9—H92⋯O4	0.89 (4)	2.00 (4)	2.879 (5)	178 (6)
O10—H101⋯O9i	0.86 (4)	1.91 (4)	2.746 (4)	164 (4)
O10—H102⋯O8i	0.84 (3)	2.04 (3)	2.883 (3)	174 (4)

Symmetry codes: (i) ; (ii) ; (iii) .